Assuring the legal validity of the “core” (underlying) transaction is essential to reducing agency and officer liability and increasing successful criminal prosecution. An agency’s policy, training, assessment, and supervision should prepare officers to recognize the “core” transaction in fact situations and know the lawful force choices available to them. It is imperative to understand the three legal environments officers operate within when conducting officer-citizen contacts and the legally permissible use of force in each environment. The three legal environments are voluntary contact, investigative detention, and arrest. This article provides a brief discussion of certain recurring high-risk police actions that are known for creating “force problems” within the three legal categories as well as strategies to reduce use of force and reduce officer liability. As a final analysis, for the use of force to be reasonable, the transaction that underpins the need for force must be lawful.